Methanol → N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N'-[2-[(t-butyloxycarbonyl)amino]ethyl]-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Participants

Reaction Steps

Reaction of Boc-aminoacetaldehyde (1.0 mmol) with N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (270 mg, 0.5 mmol) in the presence of sodium cyanoborohydride in methanol afforded N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N′-[2-[(t-butyloxycarbonyl)amino]ethyl]-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (248 mg, 72%). This material was then treated with trifluoroacetic acid (1 mL) in CH2Cl2 (2 mL) for 1 hour. Evaporation of the solvent afforded the primary amine in quantitative yield as the TFA salt.

Provenance & Evidence